Oxidation of transition metal complexes with 3,7-diazabicyclo[3.3.1]nonane-derived ligands [Elektronische Ressource] / vorgelegt von Máté Tarnai

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Oxidation of Transition Metal Complexes with 3,7-Diazabicyclo[3.3.1]nonane-Derived Ligands INAUGURAL - DISSERTATION zur Erlangung der Doktorwürde der Naturwissenschaftlich-Mathematischen Gesamtfakultät der Ruprecht-Karls-Universität Heidelberg vorgelegt von Máté Tarnai aus Budapest, Ungarn 2006 INAUGURAL - DISSERTATION zur Erlangung der Doktorwürde der Naturwissenschaftlich-Mathematischen Gesamtfakultät der Ruprecht-Karls-Universität Heidelberg vorgelegt von Máté Tarnai aus Budapest, Ungarn 2006 Tag der mündlichen Prüfung: 23. Juni 2006. Oxidation of Transition Metal Complexes with 3,7-Diazabicyclo[3.3.1]nonane-Derived Ligands Gutachter: Prof. Dr. Peter Comba Prof. Dr. Gerald Linti The work presented here was done between September 2002 and April 2006, under the supervision of Prof. Dr. Peter Comba at the Institute of Inorganic Chemistry, University of Heidelberg. Acknowledgements It is my pleasure to thank Prof. Dr.

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Published 01 January 2006
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Oxidation of Transition Metal Complexes with
3,7-Diazabicyclo[3.3.1]nonane-Derived Ligands







INAUGURAL - DISSERTATION
zur
Erlangung der Doktorwürde
der
Naturwissenschaftlich-Mathematischen Gesamtfakultät
der
Ruprecht-Karls-Universität Heidelberg









vorgelegt von
Máté Tarnai
aus Budapest, Ungarn

2006




























































INAUGURAL - DISSERTATION
zur
Erlangung der Doktorwürde
der
Naturwissenschaftlich-Mathematischen Gesamtfakultät
der
Ruprecht-Karls-Universität Heidelberg









vorgelegt von
Máté Tarnai
aus Budapest, Ungarn

2006














Tag der mündlichen Prüfung: 23. Juni 2006.






































Oxidation of Transition Metal Complexes with
3,7-Diazabicyclo[3.3.1]nonane-Derived Ligands




















Gutachter: Prof. Dr. Peter Comba
Prof. Dr. Gerald Linti
































The work presented here was done between September 2002 and April 2006,
under the supervision of Prof. Dr. Peter Comba at the Institute of Inorganic
Chemistry, University of Heidelberg.





Acknowledgements
It is my pleasure to thank Prof. Dr. Peter Comba to get acceptance in his research group, I
thank for his continuous guidance, scientific advice and for the interesting research topic.
I am grateful to Dr. Shigemasa Kuwata for discussions about cobalt and vanadium chemistry
and for his nice company to keep my Japanese in a good shape.
Without Dr. Alexander Prikhod´ko the magnetic measurements would not have been possible.
I am grateful for his advice with regard to ion exchange chromatography, and for that he
tolerated my neighbourhood in the lab.
I thank Dr. Carlos López de Laorden and Dr. Jochen Bautz for their ideas and comments
about catalysis experiments.
I thank Dr. Erik Schatz for his plenty of synthetic ideas.
Without the help of the computational brigade, namely (Dr.) Heidi Rohwer, Dr. Gopalan
Rajaraman, Prof. Mihail Atanasov and Dr. Bodo Martin I would have been completely lost in
the Gaussian calculations.
Special thanks to Dr. André Daubinet for his help in the force field calculations.
Thanks to Dr. Marion Kerscher and Maik Jakob for their help in my everyday little troubles.
I am really grateful for my trainee, Andrea Nies who made great efforts in vanadium
chemistry.
I express my gratitude to Dr. Marion Kerscher, Dr. Gopalan Rajaraman and (Dr.) Heidi
Rohwer for proof-reading of the dissertation and for their scientific and grammatical
comments.
Thanks also to other members of the group who made a great atmosphere in the lab:
Christoph Busche, Dr. Arunashree Panda, Dr. Rosana Ferrari-Zijlstra, Dr. Xiangming Zhang,
Prof. Kyaw Naing, Prof. Yang Kim, Dr. Karin Born, Nadine Brem, Laura Kleditsch, Martha
Matuschek, Matthias Menzel, Alexander Bentz, Björn Seibold, Dr. Vera Müller, Thomas
Schneider, Dr. Michael Merz, Dr. Kathrin Merz
Extra thanks for:
- the services of the University: mass spectrometry of the Institutes and microanalysis service
of Inorganic and Organic Chemistry for their contribution.
- Dr. Hans Pritzkow, Prof. Dr. Hubert Wadepohl for solving the crystal structures.
For financial support I express my gratitude to Universität Heidelberg (September 2002 –
March 2003), to Graduiertenkolleg 850 (April 2003 – September 2003) and Deutscher
Akademischer Austauschdienst (September 2003 – July 2006).






































Abbreviations:

NMR nuclear magnetic resonance
s singlet
d doublet
t triplet
dd doublet of doublets
J coupling constant
Hz hertz
ppm parts pro million
IR infrared (spectroscopy)
w weak
m medium
s strong
vs very strong
sh shoulder
MS mass spectroscopy
ESI electrospray ionization
CI chemical ionization
EI electron impact
FAB fast atom bombardment
MALDI matrix assisted laser desorption ionization
UV-vis ultraviolet-visible spectroscopy
ε molar absorption coefficient
DFT density functional theory
GS ground state
TS transition state
SP single point
hs high spin
is intermediate spin
ls low spin
SCF self consistent field
TZV triple zeta valence (basis set)
TZVPP tripel zeta valence plus polarization (basis set)
CV cyclic voltammetry
EPR electron paramagnetic resonance
SQUID superconduction quantum interference device
h hour
min minute(s)
d day(s)
TLC thin layer chromatography
EtOH ethanol
MeOH methanol
DMF dimethylformamide
DMSO dimethylsulfoxide
THF tetrahydrofurane
TEA triethylamine
TEAHCl triethylamine hydrochloride
RT room temperature
eq equivalent
TON turnover number